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Article Dans Une Revue Dalton Transactions Année : 2023

From ferrocene to decasubstituted enantiopure ferrocene-1,1 '-disulfoxide derivatives

Résumé

The functionalization of (R,R)-S,S '-di-tert-butylferrocene-1,1 '-disulfoxide by deprotolithiation-electrophilic trapping sequences was studied towards polysubstituted, enantiopure derivatives for which the properties were determined. While the 2,2 '-disubstituted ferrocene derivatives were obtained as expected, subsequent functionalization of the 2,2 '-di(phenylthio) and 2,2 '-bis(trimethylsilyl) derivatives occurred primarily at the 4- or 4,4 '-positions. This unusual regioselectivity was discussed in detail in light of pK(a) values and structural data. The less sterically hindered 2,2 '-difluorinated derivative yielded the expected 1,1 ',2,2 ',3,3 '-hexasubstituted ferrocenes by the deprotometallation-trapping sequence. Further functionalization proved possible, leading to early examples of 1,1 ',2,2 ',3,3 ',4,4 '-octa, nona and even decasubstituted ferrocenes. Some of the newly prepared ferrocene-1,1 '-disulfoxides were tested as ligands for enantioselective catalysis and their electrochemical properties were investigated.

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hal-04057610 , version 1 (04-04-2023)

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Min Wen, William Erb, Florence Mongin, Jean-Pierre Hurvois, Yury S. S. Halauko, et al.. From ferrocene to decasubstituted enantiopure ferrocene-1,1 '-disulfoxide derivatives. Dalton Transactions, 2023, 52 (12), pp.3725-3737. ⟨10.1039/d2dt03456e⟩. ⟨hal-04057610⟩
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